Isopropanol → HCID 13832261, compound

HRID 2291636Notes

Reaction equation

HRID 2291636 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH2:15][CH2:16][CH:17]1[O:21][C:20](=[O:22])[C:19]([O:23][CH3:24])=[C:18]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(C)C.C(OCC)(=O)C>CC(C)=O.O>[CH3:24][O:23][C:19]1[C:20](=[O:22])[O:21][CH:17]([CH2:16][C:15]([OH:3])=[O:14])[C:18]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 14102874HCID 14102874, compoundHCID 131709961Jones' reagent

Product 1

HCID 13832261HCID 13832261, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

2N Jones reagent (8 ml) was diluted with acetone (12.5 ml). To this solution was added a solution of 5-(2-hydroxyethyl)-3-methoxy-4-phenyl-2(5H)-furanone (1.25 g) in acetone (12.5 ml) at 0° C. over a period of 50 minutes. The mixture was stirred at ambient temperature for 15 minutes and isopropylalcohol (5 ml) was added thereto. The mixture was poured into a mixture of ethyl acetate and water. The organic layer was separated, washed with water and brine, and dried. Evaporation of the solvent gave 2-(2,5-dihydro-4-methoxy-5-oxo-3-phenyl-2-furyl)acetic acid (865 mg) which was recrystallized from diethyl ether.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. customdried
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8a6d3cd63950407c9a624a73aa5f128e
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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